NP-MRD: Showing NP-Card for {4-[(acetyloxy)methyl]-2,5-bis(4-hydroxy-3,5-dimethoxyphenyl)oxolan-3-yl}methyl acetate (NP0194964)

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Record Information

Version

2.0

Created at

2022-09-04 12:44:03 UTC

Updated at

2022-09-04 12:44:03 UTC

NP-MRD ID

NP0194964

Secondary Accession Numbers

None

Natural Product Identification

Common Name

{4-[(acetyloxy)methyl]-2,5-bis(4-hydroxy-3,5-dimethoxyphenyl)oxolan-3-yl}methyl acetate

Description

4,4'-[3,4-Bis(acetoxymethyl)tetrahydrofuran-2,5-diyl]bis(2,6-dimethoxyphenol) belongs to the class of organic compounds known as 7,7'-epoxylignans. These are lignans with a structure based on a 2,5-diaryl-3, 4-dimethyltetrahydrofuran skeleton. {4-[(acetyloxy)methyl]-2,5-bis(4-hydroxy-3,5-dimethoxyphenyl)oxolan-3-yl}methyl acetate is found in Peperomia pellucida. Based on a literature review very few articles have been published on 4,4'-[3,4-Bis(acetoxymethyl)tetrahydrofuran-2,5-diyl]bis(2,6-dimethoxyphenol).

Structure

MOL 3D MOL SDF PDB SMILES InChI


  Mrv1652309042214442D          

 37 39  0  0  0  0            999 V2000
    2.1434    2.0625    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
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M  END

     RDKit          3D

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M  END


  Mrv1652309042214442D          

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 20 26  1  0  0  0  0
  6 26  1  0  0  0  0
 26 27  1  0  0  0  0
 27 28  1  0  0  0  0
 28 29  1  0  0  0  0
 29 30  1  0  0  0  0
 29 31  2  0  0  0  0
  5 32  2  0  0  0  0
 32 33  1  0  0  0  0
 33 34  1  0  0  0  0
 34 35  1  0  0  0  0
 33 36  2  0  0  0  0
  3 36  1  0  0  0  0
 36 37  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0194964

> <DATABASE_NAME>
NP-MRD

> <SMILES>
COC1=CC(=CC(OC)=C1O)C1OC(C(COC(C)=O)C1COC(C)=O)C1=CC(OC)=C(O)C(OC)=C1

> <INCHI_IDENTIFIER>
InChI=1S/C26H32O11/c1-13(27)35-11-17-18(12-36-14(2)28)26(16-9-21(33-5)24(30)22(10-16)34-6)37-25(17)15-7-19(31-3)23(29)20(8-15)32-4/h7-10,17-18,25-26,29-30H,11-12H2,1-6H3

> <INCHI_KEY>
ALTXERNHGOZYNM-UHFFFAOYSA-N

> <FORMULA>
C26H32O11

> <MOLECULAR_WEIGHT>
520.531

> <EXACT_MASS>
520.19446185

> <JCHEM_ACCEPTOR_COUNT>
9

> <JCHEM_ATOM_COUNT>
69

> <JCHEM_AVERAGE_POLARIZABILITY>
53.41481914337189

> <JCHEM_BIOAVAILABILITY>
0

> <JCHEM_DONOR_COUNT>
2

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
{4-[(acetyloxy)methyl]-2,5-bis(4-hydroxy-3,5-dimethoxyphenyl)oxolan-3-yl}methyl acetate

> <JCHEM_LOGP>
1.682964264333333

> <JCHEM_MDDR_LIKE_RULE>
1

> <JCHEM_NUMBER_OF_RINGS>
3

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA>
9.604001549073736

> <JCHEM_PKA_STRONGEST_ACIDIC>
9.001941557745608

> <JCHEM_PKA_STRONGEST_BASIC>
-3.966409381425391

> <JCHEM_POLAR_SURFACE_AREA>
139.21000000000004

> <JCHEM_REFRACTIVITY>
129.83970000000002

> <JCHEM_ROTATABLE_BOND_COUNT>
12

> <JCHEM_RULE_OF_FIVE>
0

> <JCHEM_TRADITIONAL_IUPAC>
{4-[(acetyloxy)methyl]-2,5-bis(4-hydroxy-3,5-dimethoxyphenyl)oxolan-3-yl}methyl acetate

> <JCHEM_VEBER_RULE>
0

$$$$

HEADER    PROTEIN                                 04-SEP-22   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   04-SEP-22         0                                  
HETATM    1  C   UNK     0       4.001   3.850   0.000  0.00  0.00           C+0
HETATM    2  O   UNK     0       4.001   2.310   0.000  0.00  0.00           O+0
HETATM    3  C   UNK     0       2.667   1.540   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0       2.667  -0.000   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0       1.334  -0.770   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0       1.334  -2.310   0.000  0.00  0.00           C+0
HETATM    7  O   UNK     0       2.580  -3.215   0.000  0.00  0.00           O+0
HETATM    8  C   UNK     0       2.104  -4.680   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0       3.009  -5.926   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0       4.540  -5.765   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0       5.446  -7.011   0.000  0.00  0.00           C+0
HETATM   12  O   UNK     0       6.977  -6.850   0.000  0.00  0.00           O+0
HETATM   13  C   UNK     0       7.604  -5.443   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0       4.819  -8.417   0.000  0.00  0.00           C+0
HETATM   15  O   UNK     0       5.724  -9.663   0.000  0.00  0.00           O+0
HETATM   16  C   UNK     0       3.288  -8.578   0.000  0.00  0.00           C+0
HETATM   17  O   UNK     0       2.661  -9.985   0.000  0.00  0.00           O+0
HETATM   18  C   UNK     0       1.130 -10.146   0.000  0.00  0.00           C+0
HETATM   19  C   UNK     0       2.382  -7.333   0.000  0.00  0.00           C+0
HETATM   20  C   UNK     0       0.564  -4.680   0.000  0.00  0.00           C+0
HETATM   21  C   UNK     0      -0.342  -5.926   0.000  0.00  0.00           C+0
HETATM   22  O   UNK     0      -1.873  -5.765   0.000  0.00  0.00           O+0
HETATM   23  C   UNK     0      -2.778  -7.011   0.000  0.00  0.00           C+0
HETATM   24  C   UNK     0      -2.152  -8.417   0.000  0.00  0.00           C+0
HETATM   25  O   UNK     0      -4.310  -6.850   0.000  0.00  0.00           O+0
HETATM   26  C   UNK     0       0.088  -3.215   0.000  0.00  0.00           C+0
HETATM   27  C   UNK     0      -1.377  -2.739   0.000  0.00  0.00           C+0
HETATM   28  O   UNK     0      -1.697  -1.233   0.000  0.00  0.00           O+0
HETATM   29  C   UNK     0      -3.162  -0.757   0.000  0.00  0.00           C+0
HETATM   30  C   UNK     0      -4.306  -1.788   0.000  0.00  0.00           C+0
HETATM   31  O   UNK     0      -3.482   0.749   0.000  0.00  0.00           O+0
HETATM   32  C   UNK     0       0.000  -0.000   0.000  0.00  0.00           C+0
HETATM   33  C   UNK     0       0.000   1.540   0.000  0.00  0.00           C+0
HETATM   34  O   UNK     0      -1.334   2.310   0.000  0.00  0.00           O+0
HETATM   35  C   UNK     0      -1.334   3.850   0.000  0.00  0.00           C+0
HETATM   36  C   UNK     0       1.334   2.310   0.000  0.00  0.00           C+0
HETATM   37  O   UNK     0       1.334   3.850   0.000  0.00  0.00           O+0
CONECT    1    2                                                            
CONECT    2    1    3                                                       
CONECT    3    2    4   36                                                  
CONECT    4    3    5                                                       
CONECT    5    4    6   32                                                  
CONECT    6    5    7   26                                                  
CONECT    7    6    8                                                       
CONECT    8    7    9   20                                                  
CONECT    9    8   10   19                                                  
CONECT   10    9   11                                                       
CONECT   11   10   12   14                                                  
CONECT   12   11   13                                                       
CONECT   13   12                                                            
CONECT   14   11   15   16                                                  
CONECT   15   14                                                            
CONECT   16   14   17   19                                                  
CONECT   17   16   18                                                       
CONECT   18   17                                                            
CONECT   19   16    9                                                       
CONECT   20    8   21   26                                                  
CONECT   21   20   22                                                       
CONECT   22   21   23                                                       
CONECT   23   22   24   25                                                  
CONECT   24   23                                                            
CONECT   25   23                                                            
CONECT   26   20    6   27                                                  
CONECT   27   26   28                                                       
CONECT   28   27   29                                                       
CONECT   29   28   30   31                                                  
CONECT   30   29                                                            
CONECT   31   29                                                            
CONECT   32    5   33                                                       
CONECT   33   32   34   36                                                  
CONECT   34   33   35                                                       
CONECT   35   34                                                            
CONECT   36   33    3   37                                                  
CONECT   37   36                                                            
MASTER        0    0    0    0    0    0    0    0   37    0   78    0
END

View in JSmol

Synonyms

Not Available

Chemical Formula

C₂₆H₃₂O₁₁

Average Mass

520.5310 Da

Monoisotopic Mass

520.19446 Da

IUPAC Name

{4-[(acetyloxy)methyl]-2,5-bis(4-hydroxy-3,5-dimethoxyphenyl)oxolan-3-yl}methyl acetate

Traditional Name

{4-[(acetyloxy)methyl]-2,5-bis(4-hydroxy-3,5-dimethoxyphenyl)oxolan-3-yl}methyl acetate

CAS Registry Number

Not Available

SMILES

COC1=CC(=CC(OC)=C1O)C1OC(C(COC(C)=O)C1COC(C)=O)C1=CC(OC)=C(O)C(OC)=C1

InChI Identifier

InChI=1S/C26H32O11/c1-13(27)35-11-17-18(12-36-14(2)28)26(16-9-21(33-5)24(30)22(10-16)34-6)37-25(17)15-7-19(31-3)23(29)20(8-15)32-4/h7-10,17-18,25-26,29-30H,11-12H2,1-6H3

InChI Key

ALTXERNHGOZYNM-UHFFFAOYSA-N

Experimental Spectra

Not Available

Predicted Spectra

Spectrum Type	Description	Depositor ID	Depositor Organization	Depositor	Deposition Date	View
1D NMR	¹³C NMR Spectrum (1D, 25 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 100 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 252 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 1000 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 50 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 200 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 75 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 300 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 101 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 400 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 126 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 500 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 151 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 600 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 176 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 700 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 201 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 800 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 226 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 900 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum

Chemical Shift Submissions

Not Available

Species

Species of Origin

Species Name	Source	Reference
Peperomia pellucida	LOTUS Database	35616633

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as 7,7'-epoxylignans. These are lignans with a structure based on a 2,5-diaryl-3, 4-dimethyltetrahydrofuran skeleton.

Kingdom

Organic compounds

Super Class

Lignans, neolignans and related compounds

Class

Furanoid lignans

Sub Class

Tetrahydrofuran lignans

Direct Parent

7,7'-epoxylignans

Alternative Parents

Substituents

7,7p-epoxylignan
Dibenzylbutane lignan skeleton
Methoxyphenol
Dimethoxybenzene
M-dimethoxybenzene
Anisole
Phenoxy compound
Phenol ether
Methoxybenzene
Phenol
Alkyl aryl ether
Benzenoid
Monocyclic benzene moiety
Dicarboxylic acid or derivatives
Tetrahydrofuran
Carboxylic acid ester
Oxacycle
Organoheterocyclic compound
Carboxylic acid derivative
Ether
Dialkyl ether
Organic oxide
Organic oxygen compound
Carbonyl group
Organooxygen compound
Hydrocarbon derivative
Aromatic heteromonocyclic compound

Molecular Framework

Aromatic heteromonocyclic compounds

External Descriptors

Not Available

Physical Properties

State

Not Available

Experimental Properties

Property	Value	Reference
Melting Point	Not Available	Not Available
Boiling Point	Not Available	Not Available
Water Solubility	Not Available	Not Available
LogP	Not Available	Not Available

Predicted Properties

Property	Value	Source
logP	1.68	ChemAxon
pKa (Strongest Acidic)	9	ChemAxon
pKa (Strongest Basic)	-4	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	9	ChemAxon
Hydrogen Donor Count	2	ChemAxon
Polar Surface Area	139.21 Å²	ChemAxon
Rotatable Bond Count	12	ChemAxon
Refractivity	129.84 m³·mol⁻¹	ChemAxon
Polarizability	53.41 Å³	ChemAxon
Number of Rings	3	ChemAxon
Bioavailability	No	ChemAxon
Rule of Five	No	ChemAxon
Ghose Filter	No	ChemAxon
Veber's Rule	No	ChemAxon
MDDR-like Rule	Yes	ChemAxon

External Links

HMDB ID

Not Available

DrugBank ID

Not Available

Phenol Explorer Compound ID

Not Available

FoodDB ID

Not Available

KNApSAcK ID

Not Available

Chemspider ID

25938932

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

73014533

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

LOTUS database [Link]

Showing NP-Card for {4-[(acetyloxy)methyl]-2,5-bis(4-hydroxy-3,5-dimethoxyphenyl)oxolan-3-yl}methyl acetate (NP0194964)

MOL for NP0194964 ({4-[(acetyloxy)methyl]-2,5-bis(4-hydroxy-3,5-dimethoxyphenyl)oxolan-3-yl}methyl acetate)

3D MOL for NP0194964 ({4-[(acetyloxy)methyl]-2,5-bis(4-hydroxy-3,5-dimethoxyphenyl)oxolan-3-yl}methyl acetate)

3D SDF for NP0194964 ({4-[(acetyloxy)methyl]-2,5-bis(4-hydroxy-3,5-dimethoxyphenyl)oxolan-3-yl}methyl acetate)

3D-SDF for NP0194964 ({4-[(acetyloxy)methyl]-2,5-bis(4-hydroxy-3,5-dimethoxyphenyl)oxolan-3-yl}methyl acetate)

PDB for NP0194964 ({4-[(acetyloxy)methyl]-2,5-bis(4-hydroxy-3,5-dimethoxyphenyl)oxolan-3-yl}methyl acetate)

3D PDB for NP0194964 ({4-[(acetyloxy)methyl]-2,5-bis(4-hydroxy-3,5-dimethoxyphenyl)oxolan-3-yl}methyl acetate)

SMILES for NP0194964 ({4-[(acetyloxy)methyl]-2,5-bis(4-hydroxy-3,5-dimethoxyphenyl)oxolan-3-yl}methyl acetate)

INCHI for NP0194964 ({4-[(acetyloxy)methyl]-2,5-bis(4-hydroxy-3,5-dimethoxyphenyl)oxolan-3-yl}methyl acetate)

Structure for NP0194964 ({4-[(acetyloxy)methyl]-2,5-bis(4-hydroxy-3,5-dimethoxyphenyl)oxolan-3-yl}methyl acetate)

3D Structure for NP0194964 ({4-[(acetyloxy)methyl]-2,5-bis(4-hydroxy-3,5-dimethoxyphenyl)oxolan-3-yl}methyl acetate)